Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

Richter M, Schellhammer KS, Machata P, Cuniberti G, Popov A, Ortmann F, Berger R, Muellen K, Feng X (2017)

Publication Type: Journal article

Publication year: 2017

Journal

Organic Chemistry Frontiers Royal Society of Chemistry

Book Volume: 4

Pages Range: 847-852

Journal Issue: 5

DOI: 10.1039/c7qo00180k

Abstract

By the combination of 9a-azaphenalene and a perpendicularly oriented acene, we have synthesized three derivatives of a series of novel, fully-conjugated nitrogen-containing polycyclic aromatic hydrocarbons (PAHs), namely [7,8]naphtho[2′,3′:1,2]indolizino[6,5,4,3-def]phenanthridine, with an acetylene triisopropylsilyl (TIPS), phenyl or benzothiophenyl substituent. Their optoelectronic properties were studied via UV-Vis-NIR absorption, fluorescence spectroscopy and cyclic voltammetry. In addition, in situ spectroelectrochemistry was performed to investigate the optical and magnetic properties of the mono-radical cation and anion by quasi-reversible oxidation and reduction of 11-(tert-butyl)-5,17-bis((triisopropylsilyl)ethynyl)[7,8]naphtho[2′,3′:1,2]indolizino[6,5,4,3-def]phenanthridine (1a). Theoretical modelling confirmed the predominately closed-shell electronic ground state with a weak diradical character depending on the geometry.

Involved external institutions

Technische Universität Dresden DE Germany (DE) Leibniz-Institut für Festkörper- und Werkstoffforschung Dresden e.V. (IFW) / Leibniz Institute for Solid State and Materials Research Dresden DE Germany (DE) Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE)

How to cite

APA:

Richter, M., Schellhammer, K.S., Machata, P., Cuniberti, G., Popov, A., Ortmann, F.,... Feng, X. (2017). Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core. Organic Chemistry Frontiers, 4(5), 847-852. https://doi.org/10.1039/c7qo00180k

MLA:

Richter, Marcus, et al. "Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core." Organic Chemistry Frontiers 4.5 (2017): 847-852.

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